Nitric Acid → 2-Nitrotoluene

HRID 1076805Notes

Reaction equation

HRID 1076805 reaction equation
[O-]S([O-])(=O)=O.[Ca+2].[C:7]1([CH3:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N+:14]([O-])([OH:16])=[O:15].[N+](C1C=CC=CC=1)([O-])=O>C(Cl)(Cl)Cl>[N+:14]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH3:13])([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1140TolueneHCID 7416NitrobenzeneHCID 24497Calcium Sulfate

Product 1

HCID 69442-NitrotolueneYield 93.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

A 100g portion of soluble anhydrite was added to a solution of 32.9g toluene in 100 ml chloroform. Then a 22.6g portion of anhydrous nitric acid was added to the dispersion over a 30-minute period. Stirring at 25°C was continued for an additional 2 1/2 hour period. Nitrobenzene was added before the last half hour period and was used as the internal standard. Gas chromatographic analysis showed a 93.2% yield of nitrotoluene with the proportion being 49.1% ortho, 2.1% meta, and 48.8% para.

Workup

  1. customwas continued for an additional 2 1/2 hour period

Sources & evidence

ORD record
ord-11f07e1c4d70446f89e635f0db9a4c57
Source dataset
uspto-grants-1976_05
Patent number
US03957889

Reaction notes

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